diff --git a/es-app/src/main.cpp b/es-app/src/main.cpp
index 275455b9d..370a47448 100644
--- a/es-app/src/main.cpp
+++ b/es-app/src/main.cpp
@@ -409,6 +409,14 @@ int main(int argc, char* argv[])
     // Always close the log on exit.
     atexit(&onExit);
 
+    // Check if the configuration file exists, and if not, create it.
+    // This should only happen on first application startup.
+    if (!Utils::FileSystem::exists(Utils::FileSystem::getHomePath() +
+            "/.emulationstation/es_settings.cfg")) {
+        LOG(LogInfo) << "Settings file es_settings.cfg does not exist, creating it...";
+        Settings::getInstance()->saveFile();
+    }
+
     Window window;
     SystemScreenSaver screensaver(&window);
     PowerSaver::init();
@@ -492,6 +500,14 @@ int main(int argc, char* argv[])
         }
     }
 
+    // Check if the media directory exists, and if not, log a warning.
+    if (!Utils::FileSystem::isDirectory(FileData::getMediaDirectory()) ||
+            Utils::FileSystem::isSymlink(FileData::getMediaDirectory())) {
+        LOG(LogWarning) << "Warning - Games media directory does not exist "
+                "(or is not a directory or a symlink):";
+        LOG(LogWarning) << FileData::getMediaDirectory();
+    }
+
     // Generate joystick events since we're done loading.
     SDL_JoystickEventState(SDL_ENABLE);
 
diff --git a/es-app/src/scrapers/Scraper.cpp b/es-app/src/scrapers/Scraper.cpp
index d9fe7d7a2..39f2473d4 100644
--- a/es-app/src/scrapers/Scraper.cpp
+++ b/es-app/src/scrapers/Scraper.cpp
@@ -232,6 +232,14 @@ MDResolveHandle::MDResolveHandle(const ScraperSearchResult& result,
             if(it->existingMediaFile != "")
                 Utils::FileSystem::removeFile(it->existingMediaFile);
 
+            // If the media directory does not exist, something is wrong, possibly permission
+            // problems or the MediaDirectory setting points to a file instead of a directory.
+            if (!Utils::FileSystem::isDirectory(Utils::FileSystem::getParent(filePath))) {
+                setError("Media directory does not exist and can't be created. "
+                        "Permission problems?");
+            return;
+            }
+
             #ifdef _WIN64
             std::ofstream stream(Utils::String::stringToWideString(filePath).c_str(),
                     std::ios_base::out | std::ios_base::binary);
@@ -337,6 +345,13 @@ void ImageDownloadHandle::update()
     if(mExistingMediaFile != "")
         Utils::FileSystem::removeFile(mExistingMediaFile);
 
+    // If the media directory does not exist, something is wrong, possibly permission
+    // problems or the MediaDirectory setting points to a file instead of a directory.
+    if (!Utils::FileSystem::isDirectory(Utils::FileSystem::getParent(mSavePath))) {
+        setError("Media directory does not exist and can't be created. Permission problems?");
+        return;
+    }
+
     #ifdef _WIN64
     std::ofstream stream(Utils::String::stringToWideString(mSavePath).c_str(),
             std::ios_base::out | std::ios_base::binary);
diff --git a/es-core/src/Settings.cpp b/es-core/src/Settings.cpp
index 10d643855..0fdf343c1 100644
--- a/es-core/src/Settings.cpp
+++ b/es-core/src/Settings.cpp
@@ -252,7 +252,7 @@ void saveMap(pugi::xml_document& doc, std::map<K, V>& map, const char* type)
 
 void Settings::saveFile()
 {
-    LOG(LogDebug) << "Settings::saveFile() : Saving Settings to file.";
+    LOG(LogDebug) << "Settings::saveFile(): Saving Settings to file.";
     const std::string path = Utils::FileSystem::getHomePath() +
             "/.emulationstation/es_settings.cfg";